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Kendra Wilkinson Says Her ‘Unhealthy’ Relationship With Hugh Hefner Led to a ‘Problem’ With Sex
Former Playboy model Kendra Wilkinson said that her relationship with Hugh Hefner, who died at the age of 91 in 2017, left her with a lasting impact.
“I struggle still to this day with my relationships and my views on sex,” Kendra, 39, said during a March 20 appearance on the “Amy & T.J.” podcast with hosts Amy Robach and T.J. Holmes.
Kendra was only 18 years old when she became one of the Playboy founders main girlfriends in 2004, alongside Holly Madison and Bridget Marquardt. He was 78 at the time.
T.J., 47, pointed out that because Bridget was only a “teenager,” she had never been exposed to what’s considered a “healthy relationship.”
“It puts you on a certain path,” T.J. said. “What did that do to you and [how did it] shape what you thought a relationship was, should be, and the type of person you were interested in?”
“I had to go through a lot of therapy, and they looked at me and they’re like — this is the first time I’m admitting this — but they’re like, ‘You might have a little bit of a sex problem. You have a little bit of a problem when it comes to thinking of sex,’” the Girls Next Door alum explained. “I had to go through a lot of therapy, and they looked at me and they’re like — this is the first time I’m admitting this — but they’re like, ‘You might have a little bit of a sex problem. You have a little bit of a problem when it comes to thinking of sex.”
When asked what she was referencing specifically, Kendra replied, “It’s just unhealthy thoughts, like just like not really settling for like, you know, a marriage and stuff like that, which is not I wouldn’t say unhealthy.”

She continued, “I’m saying that, you know, everyone has their choices and some people want to be single, some people want to be married, some people and I’m just more of a fun idea type of person.”
Kendra eventually ended her relationship with Hugh in 2009, and when she was 23, she left the Playboy Mansion. That same year, she married former NFL star Hank Baskett and they welcomed a son together. While their marriage ultimately ended in divorce in 2018, Kendra said she still considers those days as some of “the happiest” of her life.
“It was like the golden years of my life,” Kendra confessed. “I went from the Playboy Mansion to, all of a sudden, this, like, marriage life in the blink of an eye, and it was the right timing. I found myself so bored at the Playboy Mansion. I was just like, ‘I’m ready to leave this place. I’m ready to start a family. I’m ready for, like, the Calabasas lifestyle. I was ready for that, and so it all came. I manifested it, and it came to me, and I met the perfect man, the man of my dreams.”
Even though the reality star and Hank, 42, eventually went their separate ways, Kenda said that he’s “the most amazing father” to her son and she “knows she chose right with him.”
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